2,3,3a,4,5,9b-hexahydro-4-(3-hydroxypropyl)-furano[3,2-c]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,3,3a,4,5,9b-hexahydro-4-(3-hydroxypropyl)-furano[3,2-c]quinoline
• 英文别名: 2,3,3a,4,5,9b-hexahydro-4-(3-hydroxypropyl)-furo[3,2-c]quinoline；3-[(3aS,4S,9bS)-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinolin-4-yl]propan-1-ol
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: FQGNBLGCJWXWPK-FPMFFAJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 苯胺 在 cellulose sulfuric acid 作用下， 以 乙腈 为溶剂， 反应 4.5h， 生成 2,3,3a,4,5,9b-hexahydro-4-(3-hydroxypropyl)-furano[3,2-c]quinoline 、 2,3,3a,4,5,9b-hexahydro-4-(3-hydroxypropyl)-furano[3,2-c]quinoline
  参考文献：
  名称：

  超分子碳水化合物支架催化合成四氢喹啉

  摘要：

  通过芳香胺与环状烯醇醚的高收率，高非对映选择性的天然超分子碳水化合物支架催化合成四氢喹啉衍生物。碳水化合物，纤维素和淀粉被转化为它们的磺酸衍生物，这些支架表现出有效的催化性能，以及出色的成本效益和可回收性。

  DOI：

  10.1016/j.tetlet.2009.11.057

文献信息

• InCl₃-Catalyzed Domino Reaction of Aromatic Amines with Cyclic Enol Ethers in Water:  A Highly Efficient Synthesis of New 1,2,3,4-Tetrahydroquinoline Derivatives
  作者：Jianheng Zhang、Chao-Jun Li

  DOI：10.1021/jo020131d

  日期：2002.5.1

  structural feature of many natural products. By using a domino reaction of aromatic amines and cyclic enol ethers or 2-hydroxy cyclic ether catalyzed by indium chloride in water, various tetrahydroquinoline derivatives were synthesized efficiently. Most cyclization products showed cis selectivity. The use of 2,3-dihydrofuran as the cyclic enol ether provided both higher reactivity and cis selectivity than

  四氢喹啉部分是许多天然产物的结构特征。通过在水中用氯化铟催化芳香胺与环状烯醇醚或2-羟基环状醚的多米诺反应，可以有效地合成各种四氢喹啉衍生物。大多数环化产物显示出顺式选择性。与使用3,4-二氢-2H-吡喃相比，使用2,3-二氢呋喃作为环状烯醇醚提供更高的反应性和顺式选择性。由于控制水中的螯合作用，使顺式选择性暂定合理。
• A highly efficient synthesis of 1,2,3,4-tetrahydroquinolines by molecular iodine-catalyzed domino reaction of anilines with cyclic enol ethers
  作者：Xu-Feng Lin、Sun-Liang Cui、Yan-Guang Wang

  DOI：10.1016/j.tetlet.2006.03.123

  日期：2006.6

  A highly efficient method for the synthesis of 1,2,3,4-tetrahydroquinoline derivatives via a molecular iodine catalyzed domino reaction of anilines with cyclic enol ethers, such as 2,3-dihydrofuran and 3,4-dihydro-2H-pyran, is described. The reaction may proceed through an aza-Diels–Alder process between an in situ generated 2-azadiene and another equivalent of cyclic enol.

  通过分子碘催化苯胺与环状烯醇醚（例如2,3-二氢呋喃和3,4-二氢-2 H-吡喃）的分子碘催化的多米诺反应，合成1,2,3,4-四氢喹啉衍生物的高效方法进行说明。该反应可通过原位生成的2-氮杂二烯与另一当量的环状烯醇之间的aza-Diels-Alder过程进行。
• Supramolecular carbohydrate scaffold-catalyzed synthesis of tetrahydroquinolines
  作者：Atul Kumar、Suman Srivastava、Garima Gupta

  DOI：10.1016/j.tetlet.2009.11.057

  日期：2010.1

  Natural supramolecular carbohydrate scaffold-catalyzed synthesis of tetrahydroquinoline derivatives by the reaction of aromatic amine and cyclic enol ether in excellent yield with high diastereoselectivity has been developed. Carbohydrates, cellulose, and starch were converted into their sulfonic acid derivative and these scaffolds exhibit efficient catalytic properties, along with excellent cost effectivity

  通过芳香胺与环状烯醇醚的高收率，高非对映选择性的天然超分子碳水化合物支架催化合成四氢喹啉衍生物。碳水化合物，纤维素和淀粉被转化为它们的磺酸衍生物，这些支架表现出有效的催化性能，以及出色的成本效益和可回收性。
• Radical cation salts induced domino reaction of anilines with enol ethers: Synthesis of 1,2,3,4-tetrahydroquinoline derivatives
  作者：Xiao Dong Jia、Yan Ren、Cong Dde Huo、Wen Juan Wang、Xiang Ning Chen、Qiong Fu、Xi Cun Wang

  DOI：10.1016/j.cclet.2010.12.038

  日期：2011.6

  A domino reaction of anilines with cyclic and acyclic enol ethers induced by catalytic amounts of TBPA+ (5 mol%) was investigated and a series of 2,4-disubstituted-1,2,3,4-tetrahydroquinolines were synthesized. Different from cyclic enol ethers, when acyclic enol ethers were used in the reaction, they serve as surrogates of acetaldehyde, producing a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines

  研究了催化量的TBPA +（5 mol％）诱导的苯胺与环状和无环烯醇醚的多米诺反应，并合成了一系列的2,4-二取代-1,2,3,4-四氢喹啉。与环状烯醇醚不同，当在反应中使用无环烯醇醚时，它们充当乙醛的替代物，产生一系列2-甲基-4-苯胺基1,2,3,4-四氢喹啉。提出了单一电子转移机制以合理化产物的形成。
• InCl3-catalyzed reaction of aromatic amines with cyclic hemiacetals in water: facile synthesis 1,2,3,4-tetrahydroquinoline derivatives
  作者：Zigang Li、Jianheng Zhang、Chao-Jun Li

  DOI：10.1016/s0040-4039(02)02450-4

  日期：2003.1

  By using a domino reaction of aromatic amines with various cyclic hemiacetals catalyzed by indium chloride in water, tetrahydroquinoline derivatives were synthesized efficiently.

  通过使用芳族胺与氯化铟在水中催化的各种环状半缩醛的多米诺反应，可以有效地合成四氢喹啉衍生物。